Improvement of some pharmaceutical properties of DY-9760e by sulfobutyl ether β-cyclodextrin

Nagase, Yukihiko; Hirata, Mari; Wada, Koh; Arima, Hisatomi; Hirayama, Fumitoshi; Irie, Tetsumi; Kikuchi, Masahiko; Uekama, Kaneto

doi:10.1016/s0378-5173(01)00851-1

Cited by 48 publications

(38 citation statements)

References 15 publications

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“…The complexing ability and, therefore, solubility improvement by SBE-β-CD is generally higher than HP-β-CD for many drug molecules, for example, DY-9760e [29], Bentazon [30], Quercetin [31], and Piroxicam [32].…”

Section: Phase Solubility Studiesmentioning

confidence: 99%

Effects of the Preparation Method on the Formation of True Nimodipine SBE-β-CD/HP-β-CD Inclusion Complexes and Their Dissolution Rates Enhancement

et al. 2014

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Abstract. The aims of this study were to enhance the solubility and dissolution rate of nimodipine (ND) by preparing the inclusion complexes of ND with sulfobutylether-b-cyclodextrin (SBE-β-CD) and 2-hydroxypropyl-b-cyclodextrin (HP-β-CD) and to study the effect of the preparation method on the in vitro dissolution profile in different media (0.1 N HCl pH 1.2, phosphate buffer pH 7.4, and distilled water). Thus, the inclusion complexes were prepared by kneading, coprecipitation, and freeze-drying methods. Phase solubility studies were conducted to characterize the complexes in the liquid state. The inclusion complexes in the solid state were investigated with differential scanning calorimetry (DSC), Xray diffractometry (X-RD), and Fourier transform infrared spectroscopy (FT-IR). Stable complexes of ND/SBE-β-CD and ND/HP-β-CD were formed in distilled water in a 1:1 stoichiometric inclusion complex as indicated by an A L -type diagram. The apparent stability constants (Ks) were 1334.4 and 464.1 M −1 for ND/SBE-β-CD and ND/HP-β-CD, respectively. The water-solubility of ND was significantly increased in an average of 22-and 8-fold for SBE-β-CD and HP-β-CD, respectively. DSC results showed the formation of true inclusion complexes between the drug and both SBE-β-CD and HP-β-CD prepared by the kneading method. In contrast, crystalline drug was detectable in all other products. The dissolution studies showed that all the products exhibited higher dissolution rate than those of the physical mixtures and ND alone, in all mediums. However, the kneading complexes displayed the maximum dissolution rate in comparison with drug and other complexes, confirming the influence of the preparation method on the physicochemical properties of the products.

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Section: Phase Solubility Studiesmentioning

confidence: 99%

Effects of the Preparation Method on the Formation of True Nimodipine SBE-β-CD/HP-β-CD Inclusion Complexes and Their Dissolution Rates Enhancement

et al. 2014

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“…[17][18][19][20] Among these compounds, hydrophilic CyDs such as HP-b-CyD, SBE-b-CyD, and branched b-CyD have received special attention, because their toxicity is very low and aqueous solubility is very high, promising a parenteral use. [63][64][65][66][67][68] The glucuronyl-glucosyl-b-CyD (GUG-b-CyD) is a new entry of branched CyDs, which contains a carboxyl group in the branched maltosyl residue. 69) In fact, the hemolytic activity of GUG-b-CyD on rabbit erythrocytes is lower than that of b-CyD and G2-b-CyD (see Fig.…”

Section: Some Characteristics Of Cyd Derivatives As Drug Carriersmentioning

confidence: 99%

Design and Evaluation of Cyclodextrin-Based Drug Formulation

Uekama

2004

CHEMICAL & PHARMACEUTICAL BULLETIN

318

137

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“…Because CDs form inclusion complexes by encapsulating other compounds into their hydrophobic cavity, natural and chemically modified CDs are widely used as pharmaceutical and food additives. Many studies of CD inclusion complex formations have been conducted to improve physicochemical properties of drugs, such as poor water solubility, [7][8][9][10] degradation upon heating [11][12][13][14][15] or by light irradiation, [16][17][18][19] and oxidation. 20) However, most of these studies have examined the effect of a single type of CD.…”

mentioning

confidence: 99%

Formation of the Ternary Inclusion Complex of Limaprost with α- and β-Cyclodextrins in Aqueous Solution

Inoue

Sekiya

Yamamoto

et al. 2015

CHEMICAL & PHARMACEUTICAL BULLETIN

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The inclusion mode of Limaprost in the presence of α-and β-cyclodextrins (CDs) was investigated to gain insight into the stabilization mechanism of Limaprost-alfadex upon the addition of β-CD in the solid state. The inclusion sites of α-and β-CDs were studied by NMR spectroscopic and kinetic methods. With the addition of α-and β-CDs, displacements in 13 C chemical shifts of prostaglandin F 2α (PGF 2α ) were observed in the ω-chain and the five-membered ring, respectively, of the drug. Similar shift changes were observed with the addition of both α-and β-CDs. In two-dimensional (2D) 1 H-NMR spectra, intermolecular correlation peaks were observed between protons of PGF 2α and protons of both α-and β-CDs, suggesting that PGF 2α interacts with α-and β-CDs to form a ternary complex by including the ω-chain with the former CD and the five-membered ring with the latter. In kinetic studies in aqueous solution, Limaprost was degraded to 17S,20-dimethyl-trans-Δ 2 -PGA 1 (11-deoxy-Δ 10 ) and 17S,20-dimethyl-trans-Δ 2 -8-iso-PGE 1 (8-iso). The addition of α-CD promoted the dehydration to 11-deoxy-Δ 10 , while β-CD promoted the isomerization to 8-iso, under these conditions. In the presence of both α-and β-CDs, dehydration and isomerization were also accelerated, supporting the formation of the ternary Limaprost/α-CD/β-CD complex.Key words Limaprost alfadex; α-cyclodextrin; β-cyclodextrin; ternary inclusion complex; NMR spectroscopy; kinetics α-, β-and γ-Cyclodextrins (CDs) are cyclic oligosaccharides in which six, seven and eight D-glucose units, respectively, are linked by α-1,4 glycosidic bonds.

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Improvement of some pharmaceutical properties of DY-9760e by sulfobutyl ether β-cyclodextrin

Cited by 48 publications

References 15 publications

Effects of the Preparation Method on the Formation of True Nimodipine SBE-β-CD/HP-β-CD Inclusion Complexes and Their Dissolution Rates Enhancement

Effects of the Preparation Method on the Formation of True Nimodipine SBE-β-CD/HP-β-CD Inclusion Complexes and Their Dissolution Rates Enhancement

Design and Evaluation of Cyclodextrin-Based Drug Formulation

Formation of the Ternary Inclusion Complex of Limaprost with α- and β-Cyclodextrins in Aqueous Solution

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